期刊
ACS CATALYSIS
卷 9, 期 12, 页码 10668-10673出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04363
关键词
nickel; catalysis; sulfinates; boronic acids; sulfones; sulfonamides; sulfonyl fluorides; sulfur dioxide
资金
- EPSRC [EP/K024205/1]
- EPSRC [EP/K024205/1] Funding Source: UKRI
We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, airstable NiBr2 center dot(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol % on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.
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